This chapter jumps to the turn of the century, when the rise of racial antisemitism fostered a new Jewish self-awareness and rendered “interracial” love and marriage central to the public debates about German Jewish identity. It analyzes three German Jewish writers of different and paradigmatic political orientations, who used love stories to diagnose the reasons for the faltering of emancipation: the assimilationist Ludwig Jacobowski, the Zionist Max Nordau, and the mainstream liberal Georg Hermann. Their works, including Jacobowski's Werther the Jew (1892), Nordau's Doctor Kohn (1899), and Hermann's Jettchen Gebert (1906), show how love stories potentially escape the ideological constraints of increasingly racialized models of identity. On the one hand, the love plot affords an opportunity to expose the obstacles encountered by Jews seeking integration in times of rising antisemitism. On the other hand, the open endings of most love stories and the ambiguous use of racial language allow the authors to eschew a final verdict on the success or failure of integration. The chapter argues that the love plot generates a host of equivocations between the social and the biological, and the particular and the universal, creating a metaphorical surplus that opens up venues to rethink the project of Jewish emancipation and assimilation.